An indirect inhibitor of Keap1-Nrf2 interactions
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2-HBA

Item No. 11879

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(1E,4E)-1,5-bis(2-hydroxyphenyl)-1,4-pentadien-3-one
CAS Number
131359-24-5
Synonyms
  • Bis(2-hydroxybenzylidene)acetone
Molecular Formula
C17H14O3
Formula Weight
266.3
Purity
≥98%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 12 mg/mlDMSO: 11 mg/mlEthanol: 14 mg/mlEthanol:PBS (pH 7.2) (1:1): 0.5 mg/ml
λmax
212, 259, 311, 373 nm
SMILES
OC1=C(/C=C/C(/C=C/C2=CC=CC=C2O)=O)C=CC=C1
InChi Code
InChI=1S/C17H14O3/c18-15(11-9-13-5-1-3-7-16(13)19)12-10-14-6-2-4-8-17(14)20/h1-12,19-20H/b11-9+,12-10+
InChi Key
YNVAHBUBGBLIEY-WGDLNXRISA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    5 mg

    $72

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    10 mg

    $134

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    50 mg

    $556

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    Product Description

    Nrf2 activation of the antioxidant response element (ARE) is central to cytoprotective gene expression against oxidative and/or electrophilic stress.1 Unless activated by inflammatory, environmental, or oxidative stressors, Nrf2 is sequestered in the cytoplasm by its repressor, Keap1.2 Because of its protective capabilities, small molecules that activate Nrf2 signaling are being examined as potential anti-cancer or anti-inflammatory agents.3 2-HBA, a synthetic analog of curcumin, is an indirect inducer of enzymes that catalyze detoxification reactions through the Keap1-Nrf2-ARE pathway. As a double Michael reaction acceptor, 2-HBA can directly modify cysteine sulfhydryl groups in Keap1 and consequently suppress Nrf2 ubiquitination, which leads to enhanced expression of antioxidative and cytoprotective enzymes.4 2-HBA doubles the specific activity of NAD(P)H:quinone acceptor oxidoreductase 1 (NQO1) in Hepa1c1c7 cells at 0.15 μM.5 In rapidly dividing mouse leukemia L1210 cells, 0.6 μM 2-HBA increases the activities of NQO1, glutathione reductase, and the levels of total glutathione.5,6 At 5-15 μM, 2-HBA causes G2/M cell cycle arrest and p53-independent, caspase 3-mediated apoptosis.5

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Wang, R., Kern, J.T., Goodfriend, T.L., et al. Activation of the antioxidant response element by specific oxidized metabolites of linoleic acid. Prostaglandins Leukot. Essent. Fatty Acids 81(1), 53-59 (2009).

    2. Gao, L., Wang, J., Sekhar, K.R., et al. Novel n-3 fatty acid oxidation products activate Nrf2 by destabilizing the association between Keap1 and Cullin3. The Journal of Biological Chemisty 282(4), 2529-2537 (2007).

    3. Taguchi, K., Motohashi, H., and Yamamoto, M. Molecular mechanisms of the Keap1-Nrf2 pathway in stress response and cancer evolution. Genes Cells 16(2), 123-140 (2011).

    4. Magesh, S., Chen, Y., and Hu, L. Small molecule modulators of Keap1-Nrf2-ARE pathway as potential preventive and therapeutic agents. Med. Res. Rev. 32(4), 687-726 (2012).

    5. Dinkova-Kostova, A.T., Cory, A.H., Bozak, R.E., et al. Bis(2-hydroxybenzylidene)acetone, a potent inducer of the phase 2 response, causes apoptosis in mouse leukemia cells through a p53-independent, caspase-mediated pathway. Cancer Lett. 245(1-2), 341-349 (2007).

    6. Dinkova-Kostova, A.T., Holtzclaw, W.D., Cole, R.N., et al. Direct evidence that sulfhydryl groups of Keap1 are the sensors regulating induction of phase 2 enzymes that protect against carcinogens and oxidants. Proc. Natl. Acad. Sci. USA 99(18), 11908-11913 (2012).